The Top 5 includes "Big Poppa/Warning," "One More Chance/Stay With Me," "Hypnotize," "Been Around the World" and "Mo Money Mo Problems," which came up at #1 on the Billboard list. All songs of the top five charted at a peak position of six or higher. "Mo Money Mo Problems" held the top spot for two weeks.

"Mo Money Mo Problems," the #1 cut on the list, was a single off of Life After Death. The song is Biggie's other posthumous #1 single, following the aforementioned "Hypnotize," which made him the only artist in Hot 100 history to have two # 1 singles after death.

"Been Around the World," the #2 song on the list, hit a peak chart position of 2 in 1998. It was a single off of Puff Daddy's 1997 album No Way Out and featured Mase along with samples David Bowie's 1983 hit song "Let's Dance" and Roy Ayers' track "Feelin’ Good."

In 1997, "Hypontize," the #3 track on the list, topped the Billboard charts for three consecutive weeks and was the first single off of Biggie's second album, Life After Death. It would become the fifth song to chart at number 1 posthumously for a credited artist. The Notorious B.I.G. was deceased by the time it hit the top spot.

"One More Chance/Stay With Me," the #4 selection on the list, hit a peak position of #2 in 1995 and is the second single on Ready To Die. The song features Faith Evans and vocals from Mary J. Blige.

Biggie's "Big Poppa/Warning," off the emcee's 1994 debut album, Ready To Die, appears on the list at #5. It would hit a peak position of 6 in 1995 and was number 1 on the rap charts. The song samples the Isley Brothers' track "Between the Sheets."